


Fatherly Guidance

by Misha_Simp



Category: Supernatural
Genre: 15x19 & 15x20 Don't Exist, Alternate Universe - Canon Divergence, Anal Fingering, Anal Sex, Barebacking, Bottom Castiel/Top Dean Winchester, Bottom Dean Winchester/Top Jack Kline, Caring Castiel (Supernatural), Castiel Teaches Jack Kline About Sex, Castiel and Dean Winchester are Jack Kline's Parents, Come Eating, Come Shot, Confused Jack Kline, Cute Jack Kline, Dean Winchester Likes It Rough, Dean Winchester Teaches Castiel About Sex, Dean Winchester Teaches Jack Kline About Sex, Dom Dean Winchester, Dominant Dean Winchester, Established Castiel/Dean Winchester, Father Figures, Father-Son Relationship, Fingerfucking, Fix-It of Sorts, Fluff and Smut, Gentle Castiel (Supernatural), Gentle Sex, Group Sex, Hand Jobs, Jack Kline & Dean Winchester Bonding, Jack is a Tease, Loss of Virginity, M/M, Masturbation, Moaning, Multi, Naive Jack Kline, Plot What Plot/Porn Without Plot, Possessive Dean Winchester, Pseudo-Incest, Rough Sex, Sex Education, Sub Castiel (Supernatural), Submissive Castiel, Threesome - M/M/M, Top Castiel (Supernatural), Top Castiel/Bottom Jack Kline, Top Jack Kline/Bottom Castiel, Top/Bottom Versatile Castiel (Supernatural), Top/Bottom Versatile Dean Winchester, Vers Castiel, Vers Dean Winchester
Language: English
Status: In-Progress
Published: 2021-01-04
Updated: 2021-01-04
Packaged: 2021-03-10 01:14:56
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,195
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27925849
Author URL: https://archiveofourown.org/users/Misha_Simp/pseuds/Misha_Simp
Summary: CW: This story includes sex between Jack, Castiel, and Dean. If that makes you uncomfortable, do not read!I am not marking this as underage because I do not view Jack as a child, I view Jack as at least 18.Castiel and Dean teach Jack about sex.P.S. Currently unfinished, that's why Dean isn't present yet.
Relationships: Castiel/Dean Winchester, Castiel/Jack Kline, Castiel/Jack Kline/Dean Winchester, Jack Kline/Dean Winchester
Comments: 2
Kudos: 17





	Fatherly Guidance

**Author's Note:**

> Once again, this story contains sex between Jack, Castiel, and Dean. This is your final warning!

Cas and I see Sam and Dean off on their hunt, despite Dean’s complaining about staying in, before returning to the bunker. Cas goes to look into other cases and I return to my room. Bored, I pull out my laptop planning to watch something on Netflix. I hesitate for a moment, remembering a previous conversation, I instead search "Busty Asian Beauties" and click the first result. A video begins playing, three women sit around a man on a couch, all four of them nude. The women are touching the man's penis as he fondles them. I stare at the video, confused at its purpose, I know sex is how humans reproduce but this seems different. I can't understand why Dean suggested this site to me, he just said I’ll need it because I’m male. He didn’t explain any further, just implied it would be good for me. I feel a pressure in my jeans as my penis, or my dick as the women in the video call it, grows. This has happened a few times before, but Sam never tells me what it means when I ask. Pausing the video, I stand and remove my pants to relieve the uncomfortable tightness. I stare down at my dick, willing it to soften, but it doesn't. Remembering the man in the video, I place my hand around the base, my grip tight, I feel the soft hairs tickle my palm. I feel a pleasant sensation shoot through me causing me to let out a small moan.  
I remove my hand, shocked at the sound that escaped my mouth, but before I have time to process it, there's a light knock on my door. From the other side, Cas calls out "Jack, may I come in? I think I found a case." Distracted by what I'm feeling, I answer without thinking "Yeah... come on in." I turn towards the door as it opens and Cas steps inside. He briefly glances down at my dick and his face reddens as he turns and goes to step out, "I'll uh... come back later." Breaking from my trance, I take a step towards him and call out, "Cas! Wait! I uh..." He stops but doesn't turn around, "Yes, Jack?" I take a few moments to contemplate what I'm about to say, "Cas, I don't know what this means. Sam and Dean won't tell me why it happens or what to do about it. Can you… can you explain it?" Cas takes a deep breath as he turns back towards me, and begins to speak, "I can't really explain it through words since its a bit complicated," he pauses, glancing down at my dick again, then resumes “but I can… help you take care of it, if you’d let me that is.” A smile spreads across my face as I take an eager step forward, "Yes! Please! It takes so long to go away on its own!"  
Cas flushes red as he removes his trenchcoat and suit jacket. He takes a step forward, now directly in front of me, he looks away as he speaks, "I... think it would be best if you took off your shirt too." Without much thought, I comply and take it off, the cool air making my nipples harden. He takes a step behind me, wrapping my left arm around his shoulder and wrapping his right around my side, his hand on my chest. He reaches his left hand around my waist, but hesitates for a moment before speaking, "I'm going to touch your dick now, is that okay?" I look him in the eyes and nod firmly, but he looks away, "Say it. I need to hear you say that this is okay." I reach up and turn his head towards me, making eye contact again, "It's okay, Cas. I trust you." His eyes linger on mine, deep cerulean searching baby blue, looking for any trace of doubt. He smiles, nodding at me, then I feel his hand wrap gently around my dick, his thumb brushing against the tip softly. The same pleasure as before takes over as my legs go weak and I lean into Cas' arms, a moan escaping once more. "C-Cas, that felt so good, please do it again!" He complies, rubbing his thumb side to side on the tip, then he begins stroking the shaft, alternating between the two. My grip on Cas' shoulder tightens as I try to keep my balance, moaning all the while. Cas moves his mouth near my ear, whispering, "It's okay Jack, I've got you." I feel two of his fingers pinch my nipple, gently tweaking it between them. I inhale sharply at the sensation before moaning his name loudly, my legs give out beneath me, but Cas holds me up. Quickly letting go of my dick, he wraps his arm under my legs, carrying me to my bed, where he sits down, placing me between his legs. I lean back into him, placing my hands on his thighs, as he returns his hands to their previous tasks, this time faster and more forceful. I feel his dick, just as hard as mine, but still confined by his pants, pressed to my lower back. I feel a knot forming in my stomach as my balls tighten, my breathing getting heavy yet shallow. Cas whispers in my ear, "I've got you Jack… you're almost there... let it all out, cum for me Jack." My back arches slightly and I screw my eyes shut, my grip tightens on his thighs as I call out, "C-Cas- yes! Cas please!" I feel bliss spread throughout my body as a warm liquid shoots from my dick, coating my chest and Cas' hand. Cas continues stroking my dick as he whispers, "There you go baby, I hope that feels good... I promised I'd take care of you... like a father." Cas slows his stroking as my mind comes back to me, my breathing slows. Cas grabs some tissues from my bedside table and begins cleaning me off as I lay spent in his lap.  
He picks me up off his lap, gently laying me on my bed. I look up at him with a smile, "Thanks Cas, that felt amazing, I... I didn't know that was possible." Cas pulls my blanket over me, "I'll do whatever you need Jack. Anytime you need me, I'll be there. I promise." He places a kiss on my forehead, then turns to walk out, noticing the strain of his pants, I grab his arm, "Wait, what about you? I... I want to make you feel like that." Cas chuckles and grabs my hand, "Thank you for the offer Jack, but I can handle it myself, you're exhausted so get some rest." I look up at him with a frown, but don't protest knowing he's right. Cas let's go of my hand and grabs his coat and jacket, heading towards the door, and with a smile he flicks off the light and closes the door. I close my eyes and drift to sleep, the feeling of Cas' hands on my body the only thing on my mind.


End file.
